Gray's performance in office has been steady but not splashy. However, his winning campaign is the subject of a federal investigation that leaves his political future uncertain. So far, three former aides have pleaded guilty to felonies.
Meanwhile, former Mayor Adrian Fenty left a tangible legacy, and his accomplishments and shortcomings are still being debated.
Fenty got national attention for his commitment to improving the District of Columbia's failing public schools. He went on a construction spree, cutting the ribbon on new school buildings, libraries and recreation centers. And he installed new bicycle lanes all over the city—including on Pennsylvania Avenue between the Capitol and the White House.
Fenty's failure to win re-election had less to do with his accomplishments than his style. He was brusque and aloof, alienated many key supporters and was never embraced in poor, predominantly black communities where Gray won by huge margins.
Many political insiders still bristle at Fenty's personality. But they agree he got things done.
"The initiatives that he sponsored are now driving the agenda," said Johnny Allem, a veteran of many local campaigns and longtime aide to former Mayor Marion Barry who supported Gray in 2010.
Two years after Gray took office, the city is in better shape financially, the commercial real estate market is booming, and 1,100 new residents are moving into the district each month. But unlike Fenty, he lacks a defining initiative or issue. Asked what his top priority is, he lists five: fiscal stability, job creation, economic development, public safety and education.
Gray declined to compare himself to Fenty, but he said the issues he's taken on are knottier than the priorities of previous city leaders.
"People talk about low-hanging fruit. Well, let somebody else pick the low-hanging fruit. We pick the hard problems," Gray said last week. "I'm not going to pick one thing."
But for many voters, education—what had been Fenty's signature issue—is the issue that trumps everything. College-educated parents obsess over whether the city's schools are good enough for their children, while parents in low-income communities often feel they have no choice but to send their children to substandard schools. Placement in the city's charter schools is determined via lottery, and not all parents have the resources to find a charter that suits their needs.
Emily Coronado, a marketing consultant who lives with her husband in the middle-class Brookland neighborhood, said the neighborhood elementary school is not a viable option for their 3-year-old son because of its poor test scores. For now, their plan is to enter the charter school lottery every year and hope for the best.
"A lot of my friends are really stressed out about it," said Coronado, who voted for Gray. "The way I look at it is that if it doesn't work out, we will have to leave or I will have to change my lifestyle."
Susan Chun, a 41-year-old federal employee who also lives in Brookland and voted for Fenty, said she's considering moving out of the district in a few years so that she can send her 3-year-old son, Alexander, to public schools. Although she's not sure if she would have committed to staying if Fenty were still mayor, she thought the city and the school system were heading in the right direction under him. She said Gray has been less aggressive about education reform.
"I'd probably be more optimistic and positive about by the time Alexander hit second grade, that there'd be more good options for him," Chun said. "Now, I'm less optimistic."
While few doubted Fenty's commitment to education, whether his policies succeeded remains an open question. His schools chancellor, Michelle Rhee, fired nearly 1,000 teachers and muscled through a new labor contract that evaluates teachers based on student performance. But the district's scores on the federal National Assessment of Educational Progress showed little improvement from 2009 to 2011. And Rhee is still dogged by questions about whether cheating was responsible for higher test scores, although several investigations have found no evidence of widespread cheating.
For all the attention Fenty's education platform drew, not everyone thinks it helped the city's schools. Former Mayor Barry, now a councilmember whose ward includes some of the lowest-performing schools in the district, said Fenty did little more than modernize school buildings.
"Test scores show that nothing significant is happening" in schools with high percentages of children living in poverty, Barry said. "At the rate we're going, it will be 20 years before we get some schools up to proficiency."
Even some Fenty supporters think Gray has done a satisfactory job. Patrick Mara, a school board member and Republican candidate for D.C. Council who's counting on Fenty supporters to back him, thinks Gray and Rhee's successor, Kaya Henderson, deserve credit for continuing to push for accountability in the school system.
"In September of 2010, I was expecting the worst. I was trying to get Fenty to run as a Republican so he would stay on the ballot in the general election," Mara said. "Gray, to his credit, has stayed out of the way, for what I see."
Political consultant Chuck Thies said that when Gray took office, there was no obvious, glaring issue to tackle. While Gray is running the city efficiently, he's become defined by scandal, Thies said.
The low point came last summer, when a former aide and close friend pleaded guilty to funneling $650,000 in illicit contributions into Gray's campaign. U.S. Attorney Ronald Machen called the effort a "shadow campaign" and said it tainted Gray's victory, and three members of the D.C. Council called on Gray to resign. The investigation continues, and Machen is clearly targeting Gray, who has denied wrongdoing.
Following the revelations about the campaign, columnist Clinton Yates wrote in The Washington Post that he was embarrassed to be a district native.
"Adrian Malik Fenty, please come back," he wrote. "The city needs you."
But since then, the federal probe has made no visible progress, and Gray has pressed forward with his multi-pronged agenda. This week he gave a State of the District speech that some observers interpreted as the opening salvo of a re-election campaign. Gray has not said whether he plans to run for a second term.
Fenty, on the other hand, has shown no inclination to return to local politics. He did not respond to a request for comment for this article.
William P. Lightfoot, a former councilmember who chaired both of Fenty's campaigns, said Fenty's legacy—warts and all—is secure.
"People believed Adrian was doing well. They just didn't like him. People still believe he did a good job, and they still don't like him," Lightfoot said. "What has changed is the disappointment in Vince Gray."
Follow Ben Nuckols on Twitter at https://twitter.com/APBenNuckols.